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Compound 1 (C5H6O) is not chiral and has an infrared absorption at 1704 cm-1. Compound 1 reacts with methyllithium to give a racemic mixture of two chiral compounds. Hydrogenation of the racemic mixture gives compound 2 (C6H12O) which, like compound 1, is not chiral.
Choose the answer for structure 1 that is consistent with this data.